8 Interesting Interview Questions from CEOs and Why They’re Asked

James Todd

January 31, 2018

Recruiters, Recruiting & Hiring, Selection Process

The interview is often the first time that a candidate will get an accurate insight into what the company is all about. From how they are greeted at reception to the questions that are asked by the hiring manager, this is all reflective of your employer brand.

Whilst it’s important to remember that interviews are not exams, asking some really smart questions provide much better insights than anything a CV can provide; such as how the candidate handles problem-solving, how they articulate their thoughts and what really makes them tick.

With that, CEOs and hiring managers are becoming more creative with their questioning. Here are 8 interesting interview questions used by hiring managers and their reasoning behind them.

‘Tell me, who is *insert interviewee name*?’

Ryan Bonnici, Director of Marketing, APAC at HubSpot

Why:

I love opening up the interview with this question since it’s incredibly open-ended. What I’m looking for in their response is:

Do they ask for clarification?

Do they jump in and start talking, or do they ask for clarification? Neither is right or wrong, each tells me more about how they would be to work with. If they ask for clarification, they might be more naturally suited to a role that is more analytical, favouring precision over speed (e.g. Marketing Analyst). If they confidently jump straight in – and are not fazed by the ambiguity of the question – they might be more naturally suited to a role that requires interpersonal skills.

What is the focus of their content?

Do they talk predominantly about who they are at work, outside of work, or both? What I look for in their response is symmetry between their interests and attitude both in and out of the workplace, to gain an insight to their personality. While there isn’t a textbook response to this, I think candidates whose responses highlight elements of work and life tend to work well with my team. It’s important to me that my team knows the organisation cares about their interests both in and outside the workplace and respects their work/life balance. Furthermore, references to life outside of the workplace are indicative that candidates understand the requirements to connect socially with team members, contributing to a strong workplace culture.

How do they close off their answer?

Does the candidate wrap the question up confidently, or ask whether they answered the question appropriately? This response provides a greater insight into the candidate and their requirements for feedback. I personally seek ongoing feedback from my team and challenge my team to do the same. A candidate whose response invited me to share information about myself or discuss whether we have mutual interests –anything at all – shows to me that they’re open to two-way dialogue around these things.

The subject matter isn’t important – I want to see how people think on their feet and communicate. I’ve had responses about International Law, startups and the structure of a novel. Traditionally, law is characterised by incomprehensible jargon that alienates many clients. We are committed to democratising legal services through our free documents and articles and we need to be able to communicate with a broad church of people. We don’t want our employees using latin maxims or overcomplicating concepts when speaking with clients.

‘What excites you?’

Nick Molnar, co-founder and CEO of Afterpay

It’s a very open-ended question which is what makes it so interesting. You learn a lot about people through the answers they provide. Do they talk about something personal or professional? Are they engaged by intellectual or physical challenges? Are they passionate about many things, one thing, or nothing? Usually, you get a strong sense of cultural fit from the answer to this question and you learn something interesting about the person you’re meeting.

If you could be or do anything, starting tomorrow, what would it be?

Tony Wu, Head of Growth at Weploy

I’m very interested in knowing what type of person I’m dealing with and by understanding this question, I’m able to understand consistencies in the rest of their answers.

‘If you were an animal, which animal would you be?’

Stormy Simon, President of Overstock

The animal kingdom is broad, and everyone can identify with a specific animal they think embodies their own personalities and characteristics,

‘There are so many different human traits, wherein the animal kingdom they put themselves, and why, really gives insight to the person answering the question. For example, just because you love dogs doesn’t mean you would identify yourself as a dog,’ she explains.

Good answers, she says, are where the candidate picks an animal that they think truly personifies the traits that set them apart. ‘People have often chosen the same animal as other candidates, but the traits they describe have never been the same,’ says Simon. But they’re not all good answers.

‘One time an interviewee said they identified with a red panda because everyone thinks they are so cute and approachable, but it turns out they’re just really lazy. We hired the candidate anyway despite that answer, but we parted ways within three weeks. It just goes to show how important the question is.’

On a scale of one to 10, how weird are you?

Tony Hseih, CEO of Zappos

One of Zappos’ core values is to ‘create fun and a little weirdness,

To make sure he hires candidates with the right fit, Hsieh typically asks the question: ‘On a scale of one to 10, how weird are you?’ He says the number isn’t too important, but it’s more about how people answer the question. Nonetheless, if ‘you’re a one, you probably are a little bit too straight-laced for the Zappos culture,’ he says. ‘If you’re a 10, you might be too psychotic for us.’

Another question Zappos usually asks candidates is: ‘On a scale of one to 10, how lucky are you in life?’ Again, the number doesn’t matter too much, but if you’re a one, you don’t know why bad things happen to you (and probably blame others a lot). And if you’re a 10, you don’t understand why good things always seem to happen to you (and probably lack confidence).

‘Are you the smartest person you know?

Larry Ellison, CTO & Chairman of Oracle.

Larry Ellison makes a point of only hiring exceptionally talented and extremely intelligent employees, and consequently coached his coached his recruiters to ask new college graduates this question.

If the candidate answered ‘yes,’ they’d get hired. If they answered ‘no,’ the recruiter would ask, ‘Who is?’ Then they’d try to hire that other person instead, Business Insider previously reported.

According to Finkelstein, superbosses like Ellison are confident enough in their own abilities that they aren’t worried about employees outshining them, and they aim to hire people who are more intelligent than they are because those employees will challenge them to come up with better ideas and solutions to problems.

‘So I understand that we’re talking about an opportunity – what do you think?’

Matt Kaness, CEO of ModCloth

Kaness interviews every single new hire at the 350-person company (a process known within ModCloth as the “Matterview”). The candidates he speaks with have all been vetted, so his questions tend to require interviewees to do more than rehash their previous professional experiences.

“I’m really trying to understand what drives them,” Kaness says. “It’s pretty free form. I always start off every conversation, every interview with, ‘So I understand that we’re talking about an opportunity — what do you think?’“

He notes that this open-ended question really gives people the chance to display their personality in their response.

“Some people really reveal themselves to be an introvert, based on the way they say ‘yes’ and then go silent,” he told Business Insider.

Others might go on and on. It’s all up to the candidate themselves.

Kaness isn’t looking for a specific response. He just wants to get a better sense of the candidate, in order to determine whether or not they’d be a good fit at ModCloth.

“It’s really about quickly getting past the formality of an interview to really find what motivates this person, in order to make sure they really fit the culture,” he says.